John P. Calamia, Founder and President – Career Milestones

• 1990-1998 Sales leadership at Sybase. IPO in 1992. Helped grow revenues from $24M to $1B. Established market dominance in the financial services sector. 

• 1997 – First sales leader at Vignette – IPO in 1998

• 2000 – First ever VP of Sales at Riversoft – IPO in 2000. Successful $125M IPO

• 2001 Founded Calamia and Associates – Launched a boutique search firm in the post dot.com era.

• 2006 Partner, Leadership Group Executive Search – Joined an established team of industry leaders from Spencer Stuart, Korn Ferry and Stanton Chase

• 2008 Founded Oak Point Consulting – Launched a 2nd boutique firm focused on technology sales and sales leadership recruiting. Completed hundreds of placements for early and late stage startups. 

• 2024 Founded Pioneers and Legends – Created and launched a successful networking community of over 400 CXOs, Investors, and Board Advisors. 

John has strong relationships with a large network of investors, venture capital firms, and senior executives from some of the world’s most successful technology companies.

Our Mission

Our mission is to build teams of exceptional sales leaders and talent, focused on one objective: market dominance.

Our Firm

We recruit hunters and closers for all sales functions including enterprise sales, corporate sales, sales enablement, revenue operations, and channels/alliances. Our firm focuses primarily on venture or private equity backed firms with revenues of up to $1 billion in ARR.

Our Differentiation

We know what it takes to be successful and where know where to find the best sales talent. Our experience is irreplaceable when it comes to nailing the right candidate profile. We’ve been on both sides of the table—first as a sales leader in fast-growing, highly successful companies, and now as specialists in talent search.